I saw this interesting question posted at PWC, and after posting my response, it was no surprise that the majority only wear one watch at a time. Of 32 respondents, only 2 individuals wear more than one watch at the same time.

One of them wears 2 watches at the same time. One on each wrist. This reminds me of Diego Maradona who wears 2 of his signature Hublots, one on each wrist. According to El Diego he wears two watches at the same time because he wants to have one set at the time zone of his location and the other on his native Argentina. I would have thought a Hublot endorser like him would already have heard of this thing called GMT watch or a World Time watch. Anyway, I think he gets away with it because he is one crazy, bigger-than-life kind of guy.